Pros: Ya, I dont know how Chicago look like, but it sounds like you did a great job.
Cons: The textures are screwed as ToySoldier says. And that really, Really look bad. Dont use the FIT tool so much. Also dont blend Dev textures and these Realistic Textures, it looks bad.
Improvements: Better Textures. And a much better Skybox, mabye 3D.
Notes: In short, I dont like the map, but its just my opinion.
Fun: I havn't tried it yet, but I like Aim maps, and ya, the map looks ok fun to play on.
Gameplay: Hmm .. Nearly the same as Fun.
Teamplay: There is not much Teamplay in Aimmaps, if you ask me.
Sexieness: Sexieness .. Boooohh .. Again, I dont like it, most because of the textures.